Abstract
Three ganglioside molecular species, SCG-1, SCG-2, and SCG-3, were obtained from the lipid fraction of the chloroform–methanol extract of the sea cucumber Stichopus chloronotus. On the basis of chemical and spectroscopic evidence, the structures of these gangliosides have been determined to be 1-O-[(N-glycolyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (SCG-1), 1-O-[8-O-sulfo(major)-(N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (SCG-2), and 1-O-[α-L-fucopyranosyl-(1→11)-(N-glycolyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (SCG-3). The ceramide moieties were composed of heterogeneous long-chain base and fatty acid units. SCG-3 is the first type of ganglioside containing a fucopyranose in the sialosyl trisaccharide moiety. Moreover, these three gangliosides exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.
